Each day I download a single newspaper via Calibre.
I'd like to email that same newspaper to two Kindle-3's at the one time.
Each Kindle has a different user@free.kindle.com address associated with it.

At the moment, I have to send out the same attachment twice through Connect/share, then select each user@free.kindle.com address separately.

I tried setting up Calibre Sharing prefs (Sharing books by email) with a ";" between the two kindle addresses but that didn't work and gives an error. Is there another way of configuring it?

I also thought of creating a mail alias (which points to the two separate addresses) but not sure how I can do this via gmail.

I tried that, and it does work. However, it still means separate emails are sent. This doubles the number of outgoing emails (and internet usage) and there seems to be a 5 minute delay bewteen each sent item (not much, but enough when you're rushing in the mornings...)